Winter Garden Communities
Stroll up and down the streets of Historic Downtown Winter Garden and enjoy the one of a kind shops that make Winter Garden an unforgettable experience. No matter what you are looking for, there is a place for you. Bring home a piece of our small-town charm.
Make History in Downtown Winter Garden
Looking to know more about this charming little city with a juicy past? Visit one of the historic museums located right in the heart of Downtown. Plan a moment of your day to learn how Winter Garden has become a successful example of historic preservation.
Discover Fresh Picks at the Farmers Market
Repeatedly voted the best Farmers Market state- and nation-wide, the Market offers a large selection of vendors from locally grown produce, baked goods, specialty foods, to homemade soaps, artisan creations, fresh flowers, and so much more!
Arts and Entertainment
Beyond one of kind shops, award-winning dining experiences, and unforgettable events... Downtown Winter Garden is also home to an underswell of arts, culture, and creativity.
Make Time for a Whole Lot of Fun
Whether seeking adventure and new discoveries, or longing to unwind and relax surrounded by historic charm, Downtown Winter Garden has something for everyone. The enchanting small town authenticity turns back time and truly feels like a getaway.
While taking in the small-town charm as you explore Downtown Winter Garden, make sure to stop in and experience the wonders of our award-winning restaurants.
Winter Garden Communities Properties
Find a Home in Winter Garden Communities
- Bella Piazza Resort Style Living Davenport
- Clermont Communities
- Esplanade at Highland Ranch 55+ Clermont
- Heritage Hills 55+ Community Clermont
- Legacy of Leesburg 55+ Community
- Plantation at Leesburg 55+ Golf Community
- Royal Highlands 55+ Golf Community Leesburg
- Summit Greens 55+ Golf Community Clermont
- Winter Garden Communities
- Minneola Communities
- The Villages 55+ Communites
- Arlington Ridge 55+ Golf Community Leesburg
- Kings Ridge 55+ Golf Community Clermont
- Trilogy 55+ Community Groveland
- Legends Golf Community
- Winter Park